CN104458601B - A kind of fibre identification colouring agent and application thereof - Google Patents
A kind of fibre identification colouring agent and application thereof Download PDFInfo
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- CN104458601B CN104458601B CN201410610690.2A CN201410610690A CN104458601B CN 104458601 B CN104458601 B CN 104458601B CN 201410610690 A CN201410610690 A CN 201410610690A CN 104458601 B CN104458601 B CN 104458601B
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Abstract
A kind of hydroxypyrazoles fibre identification colouring agent of 1 phenyl of 3 methyl of substituted thiophene azo 5, it at least includes a kind of component A as shown in formula (I), or there is the isomer of conjugation migration in formula (I) nitrogen hydrogen, or the mixture of any component ratio composition of formula (I) and its isomer, the formula (I) is：
Description
Technical field
The present invention relates to a kind of thiophene azo pyrazolone type disperse dye, and its use differentiated as textile apparel fibers
On the way.
Background technology
Fibre identification test has in many standards including AATCC, ASTM and ISO.The annex 2 of ASTM D 123《Spin
Knit relational language standard》It is middle that textile fabric is divided into four major classes：Manufacture (artificial or synthesis) fiber, mineral fibres, animal/egg
White matter fiber and string (seed and fruit hair, bast and leaf and palm and miscellany).Fibre analysis has two main projects：
Quality and quantity.Spijkers points out that " test of quality and quantity is all necessary, and the category of individual fibers is distinguished in quality test
Property, and determine that fiber whether there is in fabric sample；Quantity test is used for determining the content of fiber in fabric." fibre identification
The work such as inspection of quality and production management and control to stages such as fiber process, weaving, printing and dyeing are particularly important, and many people are studied
And therefore produce a variety of discrimination methods, such as Birefringence Method, fluorescence method, X-ray diffraction method, infrared absorption spectroscopy, rotational line
Polarization detection method, terahertz time-domain spectroscopy, density gradient method and DTG etc..Although these analysis result degrees of accuracy are higher,
Instrument price is expensive, and needs special application software and experiment technical personnel.
The simple method such as the micro- sem observation of method, burning, chemical test, the staining test that usual laboratory uses.It is aobvious
Micro mirror observation can be used for pure spinning (being made up of a kind of fiber), blending (by constituting for two or more fibers) and (longitude and latitude that interweaves
Yarn is with different raw materials) discriminating of product, correctly natural fiber and chemical fibre can be distinguished.But to the chemical fibre party
Method resolving ability is decreased obviously and not can determine that the specific kind of synthetic fibers.Though combustion test is very simple but inaccurate, and only
Fiber, yarn and fabric suitable for single component, are not suitable for fiber, yarn and the fabric of blending constituent, or by fire prevention,
Anti-flaming and other arrangements Textile materials.Chemical test needs a set of analytical reagent with corrosivity and toxicity, as a result
Influenceed larger by operating condition, and process is cumbersome.These methods are set up for the fibre identification of single type, for blending
The discriminating of fabric is difficult to be applicable.
Paint test differentiates that fiber is a kind of fast easy to operate, speed, equipment and simple method, is according to various fibres
Dimension is different to certain chemicals tinctorial property to differentiate fiber species rapidly.Frequently with colouring agent have Wagner's reagent
With No. 1 colouring agent.It is specific sample to be put into the coloring solution of micro-boiling when differentiating, boiling 0.5~1min of dye, the time is from being put into examination
Dye liquor micro-boiling starts to calculate after sample.Remove dye liquor after having contaminated, cold water wash, dry.Can be using boiling dye 3s to wool, silk and polyamide fibre
Method, expand form and aspect difference.Determine type of fibers according to form and aspect according to compareing with standard sample after dye is good.Some effects are preferable
Colouring agent is developed, and such as HI-1 fibre identification colouring agents are total to by China Textile University and Shanghai City printing and dyeing industry company
With what is developed, formed by the dye of positive ion compounding of disperse dyes, the direct dyes of anionic property, cationic, use the reagent
Differentiate the test method of textile fabric, be listed in GB/T 13787-92 textile fabric discrimination test method colouring agent methods.Du Pont
No. 4 fibre identification colouring agents, fibre identification agent-chemical drug differentiating solvent Q and the Kayastain A of Nippon Kayaku K. K's exploitation
Also formed by different types of dyestuff blending, these dyestuffs to being contaminated on specific fiber, are allowed to that unique color is presented respectively.
The known colouring agent with certain application is all composited by various dyestuffs, complicated components.Particularly anion
Dyestuff and the dye of positive ion are compounded, prepare, storage, just use during be easy to different degrees of cohesion, be not sufficiently stable.And
And disperse dyes component therein suffers from color ability, the colouring agent of mixed dye composition on synthetic fibers and semisynthetic fibre
It is unobvious in the color distinction of different fibers, such as HI-1 fibre identification colouring agents are rubine on terylene, vinegar it is fine for it is orange,
Nylon is sauce red, acrylic fibers are pink, wool is that red lotus etc. is all red color tone, if when misoperation or insufficient dyeing, or easily
Obscure.
Garment material consumer, often by fake and forged puzzlement, it is necessary to quickly and easily differentiate under the conditions of house common
The generic and approximate content of fiber, are also difficult at present.Therefore a kind of stable performance is needed, in common fiber such as terylene, Buddhist nun
The obvious fibre identification reagent of colour development difference on the fibers such as dragon, cotton, hair, vinegar fibre, acrylic fibers, and simple to operate, it is easy to accomplish fibre
Dimension discrimination method.
Inventor seminar [(a) .W.Huang, H.F.Qian, Dyes on the Research foundation of disperse dyes structure-activity relationship
Pigm.,2008,77,446；(b)W.Huang,Dyes Pigm.,2008,79,69；(c)H.F.Qian and W.Huang,
Acta Crystallogr.C,2006,C62,o62；(d)T.Tao,F.Xu,X.C.Chen,Q.Q.Liu,W.Huang,
X.Z.You,Dyes Pigm.,2012,92,916；(e)J.Geng,T.Tao,S.J.Fu,W.You,W.Huang,Dyes
Pigm.,2011,90,65；(f)B.Hu,G.Wang,W.You,W.Huang,X.Z.You,Dyes Pigm.,2011,91,105；
(g)W.You,H.Y.Zhu,W.Huang,B.Hu,Y.Fan and X.-Z.You,Dalton Trans.,2010,39,7876；
(h)X.C.Chen,T.Tao,Y.G.Wang,Y.X.Peng,W.Huang,H.F.Qian,Dalton Trans.,2012,41,
11107；(i)H.F.Qian,Y.G.Wang,X.C.Chen,W.G.Ruan,W.Huang,Dyes Pigm.,2013,99,489；
(j) H.F.Qian, Y.G.Wang, Y.Dai, J.Geng, W.G.Ruan, W.Huang, Dyes Pigm., 2015,112,67], if
Count and synthesized a kind of new polysubstituted thiophene azo pyrazoline ketone with solvatochromic and acid-base discoloration effect
Heterocycle disperse dyes, further fading of fiber is tested and shown, the hydrogen being connected with hetero atom in the type disperse dye, different
Under fiber microenvironment (different fibers show different acid-base value differences due to the architectural difference of monomer), can be in azo and pyrrole
There is conjugation migration in oxazoline ketone interannular, form hydrazone formula and azo formula dynamic isomer, can show bright-coloured red, yellow and black,
Form and aspect span is very big, and color performance is very abundant.
Because such dyestuff has different coloring behaviors and color on each fiber, especially in the change that coloring is good
To learn be even more on synthetic fibers and show complete different form and aspect, it is believed that it is very suitable for making as fibre identification material
With.
The content of the invention
It is an object of the invention to provide a kind of common fiber and its fast and accurately fibre identification colouring agent of blending product.
Technical scheme is as follows：
A kind of substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fibre identification colouring agents, it at least includes one
There is the isomer of conjugation migration in the component A kind as shown in formula (I), or formula (I) nitrogen hydrogen, or formula (I) and its with dividing
The mixture of any component ratio composition of isomers, the formula (I) is：
Above-mentioned fibre identification colouring agent, the conjugated isomers structure of compound shown in described Formulas I is as shown in Formula II：
A kind of side for preparing above-mentioned substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fibre identification colouring agents
Method, it comprises the following steps：
Step 1, the 1- amino -2- cyano group chloro- 4- formylthiophenes of -3- are taken, dissolved with nitrosyl sulfuric acid solution, obtained deep brown
The solution of color, solid all dissolves, and obtains deep brown solution, and the consumption of nitrosyl sulfuric acid is every mole of 1- amino -2- cyano group -3-
The nitrosyl sulfuric acid solution that chloro- 4- formylthiophenes are prepared with 1.1 molar sodium nitrates；
Step 2, the concentrated sulfuric acid and phosphoric acid are taken, the phosphoric acid solution of 40% sulfuric acid are prepared with 2 ﹕ of volume ratio 3, add a little ice cube,
It is put into ice salt bath, the above-mentioned deep brown solution for preparing is added drop-wise in sulfuric acid phosphoric acid solution, the consumption of sulfuric acid phosphoric acid is every
MM 1- amino -2- cyano group -3- chloro- 4- formylthiophenes sulfuric acid phosphoric acid solution 12.5ml, quick stirring, after dripping, instead
Answer 10~15min；
Step 3,1-phenyl-3-methyl-5-pyrazolones ketone is taken, 10ml methyl alcohol and 10ml deionized waters are added with every mM
Amount add methyl alcohol and deionized water, ice salt bath, keeping temperature be less than 0 DEG C, by equimolar diazo solution obtained in step 2
It is added drop-wise in this 1-phenyl-3-methyl-5-pyrazolones ketone solution, and is quickly stirred vigorously, after completion of dropping, reacts 5~10min
It is allowed to complete；
After step 4, reaction terminate, reaction solution liquid is heated to 40~50 degree and is aged 5 minutes, dye granule is become big, subtracted
Pressure suction filtration, successively with water, the solution of 1 ﹕ of ethanol/water 1 washing, drying obtains substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxyls
Pyrazoles fibre identification colouring agent.
The preparation method of above-mentioned substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fibre identification colouring agents,
Described nitrosyl sulfuric acid solution such as laxative remedy is prepared：1mmol NaNO2, the 12mmol concentrated sulfuric acids are added, quick stirring is heated to
At 65-70 DEG C, stop heating, Temperature fall, if salting out, can somewhat heat dissolves it, obtains nitrosyl sulfuric acid.
Inventor's research finds that structure shown in formula (I) generally there are the tautomerism of azo and hydrazone formula structure, lead at room temperature
To exist with hydrazone formula configuration, and hydrazone hydrogen and pyrazolone carbonyl formed intramolecular hexa-atomic ring hydrogen bond, but the proton of hydrazone hydrogen
Under certain condition (supermolecular mechanism of such as different pH value, temperature and solvent) can pyrazolone ring, azo unit with
And migrated in thiphene ring.Just because of the characteristic that this kind of proton is migrated under certain chemical environment, they and different fibrations
When the different chemical groups that can be had by fiber influenceed, dye composition shown in formula (I) and its conjugation migration of hetero atom hydrogen
Isomers exist in different proportions, show different colors,.
Dye composition of the present invention is a class water-insoluble dye.Use for convenience, generally, the present invention
Fibre identification colouring agent in the presence of auxiliary agent through case of wet attrition, the disperse dyes product that dispersion processing Cheng Yi is used.For example will
Dye composition shown in general structure (I) and general structure (II), with sand milling in the presence of auxiliary agent, water or other wetting agents
Machine is ground, and makes its average grain diameter at 0.1 to 10 micron, obtains the disperse dyes system of fibre identification colouring agent of the invention
Product.The disperse dyes product for obtaining can be used to prepare print paste or dye bath after the addition of water.
Described auxiliary agent is dispersant, the diffusant etc. commonly used when disperse dyes are processed, preferably one of following or its is any
Several mixtures：The formaldehyde condensation products of naphthalene sulfonic acids, the formaldehyde condensation products of alkyl naphthalene sulfonic acid, the formaldehyde condensation of benzyl naphthalene sulfonic acids
Thing, lignosulfonates, polycarboxylic acid macromolecule dispersing agent, the hydrolysate of phenylethylene-maleic anhydride resin, styrene-Malaysia
The poly- second two of the ammonolysis thing of anhydride resin, the carboxylate of phenylethylene-maleic anhydride resin, poly alkylene glycol ether sulfuric ester, alkyl
The anionic dispersing agents such as alcohol phosphate.Especially naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), condensation compound of methyl naphthalene sulfonic acid and formaldehyde
(such as Dispersant MF), benzyl naphthalenesulfonate formaldehyde condensation compound (dispersing agent CNF), sodium lignin sulfonate (such as commercial dispersants Reax
83A、Reax 85A).The ratio of auxiliary agent and dye composition can change in relative broad range, generally auxiliary agent and dyestuff
Weight ratio be (0.2~10):1, preferably (0.5~2):1.
The disperse dyes product of fibre identification colouring agent of the invention is with the liquid after corpusculed, emulsifiable paste state, with spraying
Seasoning etc. be dried after powdery or graininess supply dyeing.The percetage by weight of dye composition is in flowing product
10~60%, the percetage by weight of auxiliary agent is 5~45%, and remaining is water or other synergist.The synergist is optional anti-
Freeze agent, anti-settling agent, bactericide, metal chelating agent, deep-dyeing agent, thickener, stabilizer, levelling agent, fastness elevator, defoamer with
And carrier (swelling agent) etc..The percetage by weight of dye composition is 10~60%, the weight hundred of auxiliary agent in solid dye product
Fraction is 40~90%.
Fibre identification colouring agent of the present invention stained with fibrous material and can be realized according to known method.For example, optional normal
Exist with carrier (swelling agent), conventional anionic or non-ionic dispersing agent, levelling agent, buffer, reduction preventing agent etc.
Under, dyeed by dip method by water-borne dispersions at a temperature of pH value is 4~11,95~140 DEG C；Can also be by padding
Mode applies to fabric the dye slurry containing fibre identification colouring agent, drying carried out after 180~225 DEG C hot melt fixation 15 seconds~
5 minutes；The printing paste containing fibre identification colouring agent can also be applied to fabric by the method for scraping, then be steamed by saturation
Vapour (147~176KPa, 120~140 DEG C, 10~45 minutes), superheated steam (160~185 DEG C, 4~15 minutes) or xeothermic sky
Gas (190~225 DEG C, 0.5~5 minute) carries out fixation.
When full and uniform coloring is not needed, when making fast qualitative discriminating or only making rough qualitative analysis, will can also be impregnated with
The fiber or fabric of fibre identification colouring agent of the present invention, with electric iron pressing fixation or insert microwave stove heat fixation.
Directly observed by colouring after thing clear water is rinsed well.Observed with profit, can also be by soaping or reduction cleaning
Obtain distincter tone.
Material to be identified and known materials are dyeed with bath, with condition with fibre identification colouring agent of the present invention, by contrast
Method, can increase the accuracy of fibre identification.If parallel execution coloured differently condition, such as different PH, different temperatures, difference dye
Color method carries out many condition contrast, is remarkably improved the accuracy rate of fiber recognition.
By blend fibre or fabric fibre identification colouring agent level dyeing of the present invention, in view of the vision of people is to the quick of color
Sharp sensation, according to the different colorings and coloured light of dissimilar fibers, can judge whether blending is equal with the uneven rate of testing fiber blending
It is even.If coloured fiber or fabric are chosen into a point different color under the microscope, weight is weighed in the balance respectively, with detection fibers or can knit
The blending rate of thing.
Substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fibre identification colouring agents of the invention and the present inventor
Benzisothiazole azo pyrazolines disperse dyes (CN201210498771.9) and benzisothiazole azo pyridine of preceding invention
Ketone disperse dyes (CN201210553668.X) are compared, dyestuff of the invention for different kinds of fibers form and aspect span more
Greatly, color is distincter, differentiates and is easier and accurate, meanwhile, preparation is also easy to.
Brief description of the drawings
Fig. 1 is that pH value is 4~4.5, six kinds of coloring cases of fabric；
Fig. 2 is that pH value is 7~8, six kinds of coloring cases of fabric.
Specific embodiment
The present invention is illustrated with specific embodiment below, but protection scope of the present invention is not limited to this.
Embodiment 1.
Weigh 0.227g (3.3mmol) NaNO2, add 2.5ml (39.6mmol, 1：12) concentrated sulfuric acid, quick stirring, heating
To (temperature is no more than 80 DEG C) at 65-70 DEG C, stop heating, Temperature fall, if salting out, can somewhat heat makes its molten
Solution, obtains nitrosyl sulfuric acid.(it is public that cypress medicine is breathed out in Nanjing to take the chloro- 4- formylthiophenes of 0.558g (3mmol) 1- amino -2- cyano group -3-
Department), dissolved with above-mentioned solution, then the concentrated sulfuric acid of 2ml is added, and auburn solution has been obtained, solid all dissolves.
The 5ml concentrated sulfuric acids are taken, 7.5ml phosphoric acid is made into 40% sulfuric acid/phosphoric acid solution in 250ml three-necked bottles, adds a little
Ice cube, is put into ice salt bath.The above-mentioned deep brown solution for preparing is added drop-wise in sulfuric acid solution, quick stirring, after dripping,
10~15min of reaction.
0.523g (3mmol) 1-phenyl-3-methyl-5-pyrazolones ketone (Aladdin Reagent Company) is weighed, 250ml tri- is put into
Neck bottle, adds 30ml methyl alcohol, and 30ml deionized waters, ice salt bath, keeping temperature is less than 0 DEG C, above-mentioned diazo solution is added drop-wise to
In this 1-phenyl-3-methyl-5-pyrazolones ketone solution, and quickly it is stirred vigorously, after completion of dropping, 5~10min of reaction has been allowed to
Entirely.
After reaction terminates, mother liquor is heated to 40~50 degree and is aged 5 minutes, dye granule is become big, depressurize suction filtration, successively
With water, the washing of the solution of 1 ﹕ of ethanol/water 1, drying, the quality for obtaining compound I is 0.98g (yield 88%).
Mp:295-297℃.Anal.Calcd.for[C16H10ClN5O2S]:C,51.96；H,2.71；N, 18.84%
.Found:C,51.45；H,2.53；N, 18.08%.Main FT-IR absorptions (KBr pellets, cm-1):3431
(m),2225(w),1650(s),1544(vs),1495(s),1364(s),1209(m),1136(vs).1H NMR(500MHz,
CD3CN)δ:9.99(s,1H,aldehyde),7.94-7.95(d,2H,phen),7.48-7.51(m,2H,phen),7.27-
7.30(m,1H,phen),2.37(s,3H,Me).Negative ESI-MS:M/z=370.25, [M]-.
Embodiment 2
By 2 grams of dispersant Reax 83A, the ammonolysis thing of 10 grams of macromolecule dispersing agent phenylethylene-maleic anhydride resins, 30 grams
Wetting agent and antifreeze glycol, 0.1 gram of bactericide CMIT, 0.1 gram of defoamer benzyl carbinol
Oleate and 47.8 grams of water, it is well mixed using homogenizer, add 10 grams of formulas (I-1) to mixed liquor in whipping process
Shown dye composition.Diamond dust is subsequently adding, is ground 40 hours under 3500 revs/min of rotating speed using grinder, obtained
The mill base for being uniformly dispersed, stablizing.Weigh 30 grams of mill bases, add 9 grams of ethylene glycol, 6 grams of diethylene glycol (DEG)s, 3 grams of glycerine, 0.3 gram
Surfactant A EO-9,11.7 grams of water, after being stirred under normal temperature, use aperture to be filtered for 0.45 micron of filter, obtain final product
Fibre identification colouring agent liquid product.
Embodiment 3
Dye composition shown in 50.0 grams of formulas (I-1), 70 grams of dispersant Reax 85A, 200 grams of pure water one are reinstated into sand
Grinding machine carries out corpusculed (making decentralized processing), until particle diameter is less than 1 micron, then is spray-dried, and obtains fibre identification colouring agent
Solid-state product.
Embodiment 4
The solid-state product of fibre identification colouring agent obtained in 0.05 gram of embodiment 3 and 0.075 gram of glacial acetic acid are taken, 75 millis are made into
Dye liquor is risen, wherein pH value is 4~4.5, be put into 1.0 grams of six kinds of fabrics and (meet the examination of GB 7564-7568 textile color stabilities
Test with STANDARD ADJACENT FABRIC specification (neq ISO 105-F:1985), by six kinds of vinegar fibre, cotton, nylon, terylene, acrylic fibers and wool etc.
Fiber is constituted), the fiber needle fabric of material is known at 1.0 grams of ends, in being warmed up to 130 DEG C by normal temperature in 60 minutes, is incubated 45 minutes, cold
Fabric is taken out when but to less than 85 DEG C, at 85 DEG C with sodium dithionite and naoh treatment 20 minutes, water rinse is used, dried
It is dry.Coloring case is as shown in Figure 1.
Embodiment 5
Operated by embodiment 4, it is sodium bicarbonate that wherein acetic acid substitutes, and wherein pH value is 7~8, obtains dramatically different with example 5
Colouring results, as shown in Figure 2：
In sum, differentiate that fiber is simple and quick using the present invention, it might even be possible to implement under the conditions of house, in addition, logical
The diversity contrast of fibre staining under different staining conditions is crossed, can exactly differentiate fiber.
Claims (4)
1. a kind of substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fibre identification colouring agents, it is characterized in that：It is at least
Including component A of the one kind as shown in formula (I), or there is the isomer of conjugation migration in formula (I) nitrogen hydrogen, or formula (I) and
The mixture that its isomer is constituted with arbitrary proportion, the formula (I) is：
2. fibre identification colouring agent according to claim 1, it is characterized in that：The conjugation of compound is different shown in described Formulas I
Structure body its structure is as shown in Formula II：
3. a kind of substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fibre identifications prepared described in claim 1
The method of toner, it is characterized in that it comprises the following steps：
Step 1, the 1- amino -2- cyano group chloro- 4- formylthiophenes of -3- are taken, dissolved with nitrosyl sulfuric acid solution, obtained auburn
Solution, solid all dissolves, and obtains deep brown solution, and the consumption of nitrosyl sulfuric acid is every mole of chloro- 4- of 1- amino -2- cyano group -3-
The nitrosyl sulfuric acid solution that formylthiophene is prepared with 1.1 molar sodium nitrates；
Step 2, the concentrated sulfuric acid and phosphoric acid are taken, the phosphoric acid solution of 40% sulfuric acid is prepared with 2 ﹕ of volume ratio 3, add a little ice cube, be put into
In ice salt bath, the above-mentioned deep brown solution for preparing is added drop-wise in sulfuric acid phosphoric acid solution, the consumption of sulfuric acid phosphoric acid is every mmoles
You are 1- amino -2- cyano group -3- chloro- 4- formylthiophenes sulfuric acid phosphoric acid solution 12.5ml, quick stirring, after dripping, reaction 10
~15min；
Step 3,1-phenyl-3-methyl-5-pyrazolones ketone is taken, the amount for adding 10ml methyl alcohol and 10ml deionized waters with every mM
Add methyl alcohol and deionized water, ice salt bath, keeping temperature to be less than 0 DEG C, equimolar diazo solution obtained in step 2 is added dropwise
To in this 1-phenyl-3-methyl-5-pyrazolones ketone solution, and quickly it is stirred vigorously, after completion of dropping, 5~10min of reaction is allowed to
Completely；
After step 4, reaction terminate, reaction solution is heated to 40~50 degree and is aged 5 minutes, dye granule is become big, depressurize suction filtration,
Water is used successively, and the solution of 1 ﹕ of ethanol/water 1 washing, drying obtains substituted thiophene azo -3- methyl isophthalic acids-phenyl -5- hydroxypyrazoles fine
Dimension differentiates colouring agent.
4. substituted thiophene azo-3- methyl isophthalic acids according to claim 3-phenyl-5- hydroxypyrazoles fibre identification colouring agents
Preparation method, it is characterized in that：Described nitrosyl sulfuric acid solution such as laxative remedy is prepared：1mmol NaNO2, add the dense sulphur of 12mmol
Acid, quick stirring when being heated to 65-70 DEG C, stops heating, Temperature fall, if salting out, can somewhat heat dissolves it,
Obtain nitrosyl sulfuric acid.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1671971A1 (en) * | 2004-12-15 | 2006-06-21 | L'oreal | Symmetric 4-pyridinium diazo compounds with a cationic or non cationic linking group, compositions comprising them , a dying process and kit thereof |
| CN102924960A (en) * | 2012-11-29 | 2013-02-13 | 南京大学 | Benzo isothiazole azo pyrazolone disperse dye as well as preparation method and use thereof |
| CN103087543A (en) * | 2012-12-19 | 2013-05-08 | 南京大学 | Benzoisothiazoleazopyridone disperse dye, preparation method thereof and use of benzoisothiazoleazopyridone disperse dye as fiber recognition reagent |
| CN103819928A (en) * | 2014-02-18 | 2014-05-28 | 南京大学 | Tetra-substituted thiophene azo pyridone disperse dye, preparation method and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1354005B1 (en) * | 2001-01-26 | 2011-02-23 | Huntsman Advanced Materials (Switzerland) GmbH | Azo dyes, a process for their preparation and their use in the dyeing or printing of hydrophobic fibre materials |
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2014
- 2014-11-03 CN CN201410610690.2A patent/CN104458601B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1671971A1 (en) * | 2004-12-15 | 2006-06-21 | L'oreal | Symmetric 4-pyridinium diazo compounds with a cationic or non cationic linking group, compositions comprising them , a dying process and kit thereof |
| CN102924960A (en) * | 2012-11-29 | 2013-02-13 | 南京大学 | Benzo isothiazole azo pyrazolone disperse dye as well as preparation method and use thereof |
| CN103087543A (en) * | 2012-12-19 | 2013-05-08 | 南京大学 | Benzoisothiazoleazopyridone disperse dye, preparation method thereof and use of benzoisothiazoleazopyridone disperse dye as fiber recognition reagent |
| CN103819928A (en) * | 2014-02-18 | 2014-05-28 | 南京大学 | Tetra-substituted thiophene azo pyridone disperse dye, preparation method and use thereof |
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